


A passion for learning

by queerly_it_is



Category: Supernatural
Genre: Comeplay, Crossdressing, Dirty Talk, Feminization, Fingerfucking, M/M, Sibling Incest, Teaching
Language: English
Status: Completed
Published: 2012-06-07
Updated: 2012-06-07
Packaged: 2017-11-07 04:31:27
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 1,726
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/426936
Author URL: https://archiveofourown.org/users/queerly_it_is/pseuds/queerly_it_is
Summary: <blockquote class="userstuff">
              <p>Sam asks for Dean to "teach him" how to please a girl. So Dean gives a hands on demonstration on finger fucking.</p>
            </blockquote>





	A passion for learning

**Author's Note:**

  * For [heard_the_owl (heardtheowl)](https://archiveofourown.org/users/heardtheowl/gifts).



> Written for heard_the_owl over on LJ.

Sam has that twitchy, nervous look that says he really wants to ask Dean something, but is all shy and embarrassed about it.  
  
As a good big brother, Dean is obligated to help him out.  
  
“Y’know Sammy; if you wanna take me to the prom, all you gotta do is ask.”  
  
Doesn’t mean he isn’t gonna be a dick about it, o’course. At least Sam stops squirming all over the tiny motel room furniture, little bitch was making it hard to think.  
  
“If I wanted to take you to the prom, I’d have to drown myself in holy water.” Not even the slightest pause between the blushing and the bitchface. Impressive.  
  
“Oh, I’m hurt Sammy, you don’t think I’m pretty?” Pouting, batting his eyelashes at his brother across the room.  
  
Back to blushing now, then. Interesting.  
  
“Dean. Do you. Could you maybe.” Stammering, way he _always_ does when whatever he wants to ask is about sex. This oughta be good.  
  
“C’mon Sammy, you can’t say it, you shouldn’t be doin’ it.” Trying to sound smug and all-knowing, rather than _pissed_ at the idea of Sam going off and finding someone to do sexy stuff with. Dean’s _right_ here, for fucks sake.  
  
“Howdoyoufingeragirl?” All one word, like if the kid gets the question out fast enough the blood won’t reach his face. Doesn’t really work.  
  
“One more time there, Sammy?” Dean knows _exactly_ what he said, just kinda wants to hear Sam say it again. He ignores the epic sigh and roll of fox-slanted eyes, focuses on the way he licks his pretty pink lips instead. Best part of hanging around Sam; there’s always somewhere fun to look.  
  
“How. How do you finger a girl?” And Dean’s gotta give him credit; only one pause and eye-contact all through the question.  
  
“Why d’ya wanna know that Sammy?” Something low and dangerous - predatory - in the question “You got some sweet little thing you haven’t told me about?” Sam’d _better_ say no; Dean doesn’t like hitting girls.  
  
“No!” Embarrassed again, and Dean relaxes a little. “I just. Bethany Maynard; from that school back in Kanas? She kinda. She wanted me to.” Some meaningful hand gesture, and Dean reminds himself driving straight back to Kansas to kill little Miss Maynard would be _wrong_. “And I didn’t really know how to, you know.” _Really_ blushing now, but Dean supposes it’s only natural. 

Sammy did just turn fifteen today, after all.  
  
“Ah, okay. Well, not to worry Sammy, big brother’ll help ya out.” _Way_ more innuendo than he meant to put into that, but Sam doesn’t seem to mind, way he’s wriggling on the chair again.  
  
“’Course, only real way you’re gonna understand the material is with a proper demonstration.” Sounding less like a teacher and more like a porno actor, but fuck it.  
  
He crosses to his duffel, digs right to the bottom where he hopes he still has the - _yes_. It’s a miniskirt. It was gift from a freaky little number a couple’a states back; Terry, Tricia, something with a ‘T’, Dean doesn’t remember, s’not the point, anyway.  
  
Sammy’s gonna look _awesome_ in it.  
  
“Dean, what. C’mon man, no way.” He’s trying to hide the hitch in his breath, but Dean knows every tell his baby brother has; knows he’s got him on the hook now, just waitin’ to be reeled in.  
  
“Gotta do this right, Sammy.” He says, as much seriousness as he can muster with this much blood moving away from his brain. “Can’t have my little brother not knowing what to do if his lady’s in a skirt, now can I?” Yeah, ‘cos _that’s_ why Dean’s doin’ this.  
  
He flings the tiny little garment at Sam, all but shoves him into the bathroom so he can change, reminder of “No underwear, Sammy!” shouted through the wooden door.  
  
He goes back to his duffle, pulls the lube from the side-pocket, yanks the top sheets off the nearest bed, sits, and waits. And waits.  
  
“C’mon Sammy, only got three days before Dad gets back.”  
  
“I look stupid, man.” Faint reply from the bathroom. Dean _seriously_ doubts that.  
  
Sam walks outta the bathroom, and every bit of blood in Deans body floods into his dick so fast he actually gets light-headed. Jesus fucking _Christ_.  
  
Sam is naked, except for the little green skirt; long, _long_ legs bared up nearly to his crotch, lithe, compact muscle and caramel skin _everywhere_ , hair flopping in his face, chest heaving slightly with every breath, teeth clamped firmly onto his lower lip.  
  
Dean tries not to come, right then and there.  
  
“Lookin’ good, Sammy.” Voice like he’s been chain-smoking, Dean holds out a hand and Sammy walks over, quiet and meek, which _really_ doesn’t help. He stands between Dean’s legs where he’s kinda slumped back on the bed, and Dean runs a hand from the waistband of the skirt up as high as his arm will reach, fingertips barely reaching Sam’s shoulder.  
  
Other arm going ‘round Sam’s waist, Dean _tugs_ and gets his baby brother underneath him, spread out on the bed. Coltish limbs everywhere, bulge clearly showing under the skirt, dark, secret place between his legs.  
  
 _Fuck._  
  
The snick of the cap on the lube gets Sam’s eyes on his, pupils seriously blown, breath coming harder, deep-red staining halfway down his chest.  
  
“S’okay Sammy. Gonna take care of you.” Running one hand up and down Sam’s left leg - reminds himself about waxing, for next time - he squeezes a decent amount of lube into his right palm, and tries to remember how to _talk_.  
  
He’s supposed to be teaching Sam, after all. 

“First thing you gotta do, is relax her a little.” Runs his non-slick hand up Sam’s thigh, under the skirt, feels the muscles relax as his breath pushes out in a broken sigh.  
  
“Always start slow, just ease her into it.” Slick finger circling the _tight_ little place between Sam’s legs, bypassing his more than half-hard cock altogether.  
  
Sam _is_ playing a girl right now, after all.  
  
The muscle relaxes, quicker than he’d expected - sudden flash of Sam doin’ this to himself in the shower making him groan - and his index finger slips in to the first knuckle.  
  
“ _Fuck_ , that’s it Sammy, open up for it so _nice._ “ Sam moans, eyes squeezed shut, dick totally hard now.  
  
Finger working in a little deeper, Dean uses his other hand to spread Sam’s legs wide as he can “C’mon baby boy, know what you want, know just what you can take.” Doesn’t register half of what’s coming out his mouth now, just talking for the way it makes Sam wriggle on his hand.  
  
“Fuck, there ya go, that’s one all the way in, Sammy. How’s it feel, huh?” Fingertip pressing hard against that _spot_ inside.  
  
“S‘fuckin‘ _good_ Dean, _God_.” Hips pushing down into Dean’s hand, impressive bulge twitching beneath the skirt.

“You want another one, Sammy?” Running the tip of his middle finger around Sam’s pucker where it’s stretched and clenching a little.  
  
“Yeah. C’mon Dean, I. I want it.” Pleading broken with high-pitched whines as Dean slides a second finger straight to the middle knuckle.  
  
“S’right, Sammy, gonna stretch you all out, get this little pussy all wet and messy for me.” Fingers fucking in and out, Sam opening up so sweet, hottest fucking noises coming from his throat.  
  
The squelch of lube is audible as Dean presses around his brother’s rim with a third finger, and knowing that Sam _likes_ the burn as he’s forced open just that little bit too-quick almost makes him wanna stuff Sam all the way full, watch him try to take it just for Dean.  
  
He’s aware it’s not really about the girls, anymore.  
  
He really needs to _see_ , he suddenly decides, flips the skirt up above the waistband. Sam’s fucking _perfect_ cock leaves a wet blot of precome against the almost-rough material as it slaps toward his belly, red at the tip and so so _hard_. Pretty as that is, it’s nothing compared to the sight of Sam with three of Dean’s fingers buried up in him. _Fuck_ he’s a sexy little bitch.  
  
“So pretty like this Sammy, spread out and fucked open, fingers in your little cunt. _God_ love it don’t you.” Angling to hit Sam’s prostate _just_ right with every thrust, Dean watches as Sam squirms and pushes his hips down into it.  
  
“Perfect little slut when you’re begging and all broken open. Fucking _made_ for this, baby boy.” Hand moving faster, harder, seeing if Sam can come without a hand on him. Judging from the way he’s leaking like a busted faucet; precome drooling from the almost-purple head of his dick, thin string of it connecting his cock to the fabric of the skirt, Dean’s pretty sure he _can_.  
  
“Your so fucking _wet_ Sammy, little pussy dripping.” Twist of fingers, shudder running from Sam’s hips all along him, dick twitching and leaking everywhere. “You gonna come baby? Gonna come on just my hand, thinkin’ about my _cock_.” Particularly hard thrust, and Sam flies over the edge; come shooting up his chest and landing on his neck, his stomach, the _skirt_.  
  
Dean fucks him through it, hand slowing a little, getting Sam to ride the orgasm out while his other hand fumbles at the button on his jeans, shoves them down his thighs and pulls his cock out. He withdraws his fingers, Sam making a noise of what Dean’s gonna go ahead and call _dissapointment_ , and jerks himself off with the warm, wet slick still covering his hand.  
  
“Gonna mark you up Sammy, get my come all over you.” Getting close already, way too long trapped in his jeans while he focused on Sam.  
  
“Yeah” weak croak, throat working as he swallows. “Mess me up, Dean.” Fuck that is _it_. He shoots over Sam’s legs, his cock, some mixing with the mess already on his brother’s belly. He watches his come run down behind Sam’s balls, joining the shiny-wet covering his thighs and leaking out of him where he‘s all loose and open.  
  
He runs a hand through the mess, spreads it into Sam’s skin. Drags him up and kisses the breath out of him, tasting and savouring the sweet flavour of his mouth. Need for air forcing him back a little, he presses his forehead to his brother’s, speaks low and soft.  
  
“Happy birthday, Sammy.” 


End file.
